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Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions.
Bioorg Chem. 2017 10; 74:104-114.BC

Abstract

In this study, a series of novel bromophenols were synthesized from benzoic acids and methoxylated bromophenols. The synthesized compounds were evaluated by using different bioanalytical antioxidant assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+) radical scavenging assays. Also, reducing power of novel bromophenols were evaluated by Cu2+-Cu+ reducing, Fe3+-Fe2+ reducing and [Fe3+-(TPTZ)2]3+-[Fe2+-(TPTZ)2]2+ reducing and ferrous ions (Fe2+) chelating abilities. The compounds demonstrate powerful antioxidant activities when compared to standard antioxidant molecules of α-tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT). Also in the last part of this studies novel bromophenols were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II (hCA I and hCA II) isoenzymes. The newly synthesized bromophenols showed Ki values in a range of 6.78±0.68 to 126.07±35.6nM against hCA I, 4.32±0.23 to 72.25±12.94nM against hCA II, 4.60±1.15 to 38.13±5.91nM against AChE and 7.36±1.31 to 29.38±3.68nM against BChE.

Authors+Show Affiliations

Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey. Electronic address: amaras@atauni.edu.tr.Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey. Electronic address: sgoksu@atauni.edu.tr.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28772158

Citation

Öztaskın, Necla, et al. "Novel Antioxidant Bromophenols With Acetylcholinesterase, Butyrylcholinesterase and Carbonic Anhydrase Inhibitory Actions." Bioorganic Chemistry, vol. 74, 2017, pp. 104-114.
Öztaskın N, Taslimi P, Maraş A, et al. Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. Bioorg Chem. 2017;74:104-114.
Öztaskın, N., Taslimi, P., Maraş, A., Gülcin, İ., & Göksu, S. (2017). Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. Bioorganic Chemistry, 74, 104-114. https://doi.org/10.1016/j.bioorg.2017.07.010
Öztaskın N, et al. Novel Antioxidant Bromophenols With Acetylcholinesterase, Butyrylcholinesterase and Carbonic Anhydrase Inhibitory Actions. Bioorg Chem. 2017;74:104-114. PubMed PMID: 28772158.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. AU - Öztaskın,Necla, AU - Taslimi,Parham, AU - Maraş,Ahmet, AU - Gülcin,İlhami, AU - Göksu,Süleyman, Y1 - 2017/07/20/ PY - 2017/06/10/received PY - 2017/07/16/revised PY - 2017/07/17/accepted PY - 2017/8/5/pubmed PY - 2017/10/11/medline PY - 2017/8/4/entrez KW - Acetylcholinesterase KW - Antioxidant activity KW - Bromophenols KW - Butyrylcholinesterase KW - Carbonic anhydrase SP - 104 EP - 114 JF - Bioorganic chemistry JO - Bioorg. Chem. VL - 74 N2 - In this study, a series of novel bromophenols were synthesized from benzoic acids and methoxylated bromophenols. The synthesized compounds were evaluated by using different bioanalytical antioxidant assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+) radical scavenging assays. Also, reducing power of novel bromophenols were evaluated by Cu2+-Cu+ reducing, Fe3+-Fe2+ reducing and [Fe3+-(TPTZ)2]3+-[Fe2+-(TPTZ)2]2+ reducing and ferrous ions (Fe2+) chelating abilities. The compounds demonstrate powerful antioxidant activities when compared to standard antioxidant molecules of α-tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT). Also in the last part of this studies novel bromophenols were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II (hCA I and hCA II) isoenzymes. The newly synthesized bromophenols showed Ki values in a range of 6.78±0.68 to 126.07±35.6nM against hCA I, 4.32±0.23 to 72.25±12.94nM against hCA II, 4.60±1.15 to 38.13±5.91nM against AChE and 7.36±1.31 to 29.38±3.68nM against BChE. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/28772158/Novel_antioxidant_bromophenols_with_acetylcholinesterase_butyrylcholinesterase_and_carbonic_anhydrase_inhibitory_actions_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(17)30441-8 DB - PRIME DP - Unbound Medicine ER -